Where it all began! Big Mini Putt Club is where Billy and Allison had their first date in December 2021.

Swift & Sons is a steakhouse in the West Loop, not far from Allison and Billy's home, and their go-to place for celebrations.

Another popular go-to for Allison and Billy, Trivoli Tavern is located in a tucked-away alley and has some of the best food and vibes in the city. They highly recommend this for any of their out-of-town friends.

If you're looking for something different, check out Green Street Meats for some great BBQ, High Five Ramen for some of Chicago's most coveted ramen, or Sawada Coffee located in the same alley.

Allison and Billy love catching an off-main-stage show at the famous Second City on date night. If you're looking for a good spot beforehand, check out Twin Anchors just around the corner for a cold martini and rack of ribs (Frank Sinatra's favorite!).

Venture outside of the West Loop to Lincoln Park for this gem of a restaurant that blends British and Indian cuisine (and makes fantastic cocktails). Allison and Billy love it so much, they went here four times in a single month!

Some of the best tapas in town! Great option for brunch or dinner located in the Lincoln Park neighborhood.

Spend an afternoon at The Art Institute of Chicago, where art, history, and architecture come together in one of the city’s most iconic museums.

Bundle up for this outdoor adventure! The Chicago River architecture tour is a must-do for first-time visitors. It’s the best way to see and learn about the city’s skyline.

A quintessential Chicago photo op and an easy walk from many downtown hotels.